


Dating Dean Winchester

by doctor_detective_Winchester



Category: Supernatural
Genre: Adam is Saved, Alternate Universe - High School, Alternate Universe - Human, Castiel/Dean Winchester Cuddles, Dating, Falling In Love, First Kiss, Human Castiel, M/M, Nerd Castiel
Language: English
Status: In-Progress
Published: 2014-05-08
Updated: 2015-03-07
Packaged: 2018-01-20 19:42:15
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 4,291
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1523228
Author URL: https://archiveofourown.org/users/doctor_detective_Winchester/pseuds/doctor_detective_Winchester
Summary: <blockquote class="userstuff">
              <p>ok the timeline here is that the fire happened when the boys were a little older Sam being 4 years old and Dean being 7. Mary knew that John had cheated on her but she forgave him and when Adam's mother died giving birth to him they gladly took the baby in. So it was Adam' nursery instead of Sam's and John in his attempt to save Mary didn't get out in time. Being the closest thing to family the boys had left Bobby adopted all three of them and raised them as his own.They all grew up happy and loved. This story starts Dean's sophomore year and follows the growing relationship between him and Castiel.</p><p>I'm not really sure where this is going to end but there are a lot of fun dates I have planned for these two.  So I'm thinking maybe one date per chapter with some cliffhangers here and there just for kicks. This is my first fic so constructive criticism is always welcome!</p><p>IMPORTANT NOTE: if you read the first chapter before 5/9/14 it has been changed it's longer now</p>
            </blockquote>





	1. Asking him out

**Author's Note:**

> This is a list of grade levels and ages  
> Balthazar junior 17  
> Benny, Lisa, Jo, and Garth sophomores 16  
> Dean, Cas, Charlie, and Ash spofhmores 15  
> Sam, and Kevin seventh grade 12  
> Gabriel seventh grade 13  
> Adam and Samandriel third grade 8

"Are you serious?" Was the first thing out of his mouth he looked shocked.

"Um yeah I thought it was cool and it seemed like the kinda thing you would like . . ." Dean trailed off and let the silence stretched until Castiel squinted his eyes and tilted his head at Dean.

"You're really asking me on a date I mean you're Dean Winchester you're like the hottest guy in this whole school and you only make it worse by also being the kindest. You're the kind of guy that people dream about. Why would you want to go out with a loser like me?"  
Dean didn't say anything and the silence was soon interrupted by the bell signaling the end of their lunch period. Castiel got up to leave but Dean just fell in step with him. 

"We've both got gym now I'll walk with you." Dean offered as explanation when Castiel gave him that confused head tilt.

"Cas I asked you out because I like you I think you're really funny and its just down right adorable to see how excited you get about your um fandoms right?"  
Castiel nodded.  
"You're passionate about things and you get so happy its infectious. Why wouldn't I want to go out with you? " 

Then Dean smiled that smile where the sides of his oh so green eyes crinkled just so and every freckle seemed more prominent. That smile made Castiel want to lock Dean inside his heart and keep him away from anyone who would dare remove it.

"Well it does sound pretty cool I don't think I've ever been to something like that." Cas said smiling as well.  
"Yeah over 16 hours of sci-fi and fantasy movies isn't your everyday occurrence. They're even going to show one of those Doctor who episode as a pre show extra, thats what really made me think of you. So um yeah its in a week on the 5th a Saturday. It starts at 11 but the Doctor who episode is at 9 I thought you would want to see that so is it ok if I pick you up at like 7:30 we could get some breakfast before hand and we wouldn't have to rush to get to the theater. Oh I mean if you're saying yes that is." Dean finished with a sly smile but a hopeful look in his eyes.

"You're cute when you ramble Winchester. I'll talk to my parents tonight and let you know tomorrow ok?"

"You could let me know tonight." Dean said pulling his phone out of his pocket and passing it to Cas.

"Fine if you're done putting the moves on me I have some soccer to play." Cas handed the phone back after he put his name and number in. Dean gave him a smile and finally focused on getting in to his gym clothes. He did it he asked out Castiel Novak and he had said yes not even the two lost soccer games could dampen his happiness he had a date.

After school Dean

"Dean brother you've been smiling all day I take it the boy said yes." Benny teased as they walked to pick up Sammy and Adam from the elementary school a few blocks away.

"Yeah Benny he said yes and guess who got a phone number. Me! Man this date is going to awesome I can't wait!"

"Yes Dean I know Lisa told me all about the ear full she got during Lit. I understand brother you're happy and we're happy for you but can we not talk about up your boyfriend for like five minutes."

"Spoil sport." Dean said sticking out his tongue. He would have happily continued talking about Cas but he was caught of guard by an Adam sized weight running into him. 

"Whoa easy there tiger! Hey Adam how was school?"

"It was was great Dean! We did a new science experiment today and I got mine right on the first try everybody else had to do it two or even three times!" Adam told him quite proudly.

"Really that's great kiddo! Now where's Sammy? The sooner we find him the sooner we can go home and the sooner my little scientist can have a cookie!"

"He's in the library Dean! Him and Kevin have project due soon and they need 'absolutely every freakin second they can get' that's what Sam said." 

"Come on brother lets go round up the egg heads." Benny said as he headed toward the library. 

Sure enough there was Sam and Kevin heads bent over books and passing notes to each other at the far end of the library. 

"Sammy come on you can bring Kevin home with us. Jo and Lisa are going to be at the house waiting for me soon and there's no way me and Benny will be able to catch up if they start homework without us."

"Since when do you guys really do homework and not gossip about each other's love lives. Or did I miss the memo?"

Little brat didn't even stop reading. Dean gave Benny a side ways glance and held up four fingers. They slowly made their way behind Sam and Kevin's chairs and when Dean put the last finger down they plucked Sam and Kevin from their chairs and carried them out the door.

"DEAN! I swear if you don't put us down right now I will tell Benny Lisa and Jo where you keep that diary you think I don't know about!"  
That does get Dean to put him on the ground but instead of commenting on the diary he shouts "Race ya!" And takes off with Adam on his heels and Benny a close third with a miserable looking Kevin still thrown over his shoulder. 

"Don't worry Kevin l'm coming to save you!" Sam spared one last longing look in the direction of the library and took off after his brothers and friends.

They were all tried and out of breath by the time they got to Bobby's.  
"Will you please release Kevin! Benny we have work to do."  
Benny sat Kevin on the grass before he followed dean into the kitchen. 

"Kevin come on lets get the hose well show Dean and Benny! "  
"Ok but we have to finish our project before 6:30 my mom wants me home for dinner."  
"Thats plenty of time."  
Sam began formulating a plan of attack. They were just about ready when Lisa and Jo arrived and deciding it would be better to have them fighting with them instead of against them Sam gave them a quick run through of the plan. They agreed to help and Jo was sent inside to lure Dean and Benny out.

"Dean I think Adam fell while he was playing outside. Sam asked me to come get you."  
"How many times have I told them to be careful when they play. Benny come on lets make sure he's ok."  
"Its probably just a scratch Dean. You worry too much."  
Jo let them go outside first. "ATTACK! " She called and quickly shut and locked the door. She went over to the window so she wouldn't miss anything and it was quite a show. Sam came at them with hose Kevin was launching water balloons and Lisa and Adam were armed with water guys. Dean and Benny never stood a chance. Bobby was their saving grace 20 minutes into the ambush telling them it was time for homework now and they could have a fairer water fight another day. By the time everyone was clean dry it was already 5 so Sam and Kevin locked themselves in Sam's to work with no distractions while the older teens took over the living room.

"Ok Dean spill Lisa will only tell me that he said yes I want details! "  
Dean told them how he had asked Cas out leaving out all the embarrassing parts.  
"Its about damn time boy! You've been talking about this kid like he hung the moon for weeks now. Im glad you stopped dragging your feet." They all turned toward Bobby startled.  
"Don't look at me like that I can eavesdrop if I want its my house. I better meet this boy soon Dean."  
They all laughed "Ok Bobby I'll work on that for you." After that they finally started their homework and because Bobby wasn't taking to trips everyone got in the car to be dropped off when Kevin had to leave. Dean decided texting Cas would be ok so he did.

Dean:"hey Cas! Its Dean so what's the verdict on our date?"  
Dean smiled and went back to his homework. 

After school Cas

Cas scanned the hall looking for his friends he couldn't wait to tell the news. Besides Charlie of course she got to hear all about it during art class and had all but jumped for joy.

"Look at my little bird getting ready to fly! Castiel please remember to invite me to the wedding and I better the maid of honor. Don't fight me on this child!"  
"Charlie its one date I think the wedding bells are a little far off clam down please."

Cas smiled at the memory or at least smiled bigger. He hadn't really stopped since gym and so what he was happy. Dean freaking Winchester asked him out today. Him too quite nerdy Castiel that could benign watch tv for hours a time but was hopelessly clueless when put in social situations with out his friends.

Speaking of his friends there was the mullet that could only belong to Ash talking with Charlie by her locker.  
"Ash have you heard what's up with our Cassie?"  
"Charlie No its my news I get to tell them."  
"Cas come on let me do you'll just blurt it out no finesse and this is big news it calls for a little dramatics. Please please please with a strawberry on top." She smiled sweetly and Cas considered her for a moment.  
"Charlie I thi-"  
"DEAN WINCHESTER TOTALLY ASKED OUT CASSIE OUT! "  
Cas glared at her  
"So much for me just blurting it out. Subtle Charlie real subtle."  
"I Love you too Cassie."  
"Well Ash what do you think?"  
Ash hadn't said much just watched his friend with an amused expression on his face.  
"I think its great Cas now come on Garth's dad is waiting for us outside. We gotta go."

They headed to the front of the school and piled into Mr. Fitzgeralds car.  
"Hey guys how was school?" Mr. Fitzgerald smiled at them. "Anything big happen today?"  
"Not really took a chem test turned in some homework worked on an art project Cas got asked out by the guy of his dreams. Same old same old." Cas groaned.  
"Do I get to tell anybody Charlie?"  
"Nope I have dubbed myslef the carrier of this news and it will be screamed from roof tops at my earliest convince."  
"Well Cas that exciting what's his name?"  
"Thank you Mr. Fitzgerald his name is Dean Winchester."  
"The Dean Winchester asked you out!?"  
"Well hello to you too Garth and yes the Dean Winchester asked me out as you put it. We're going to get breakfast then go to a movie marathon at the old theater downtown."  
"Well I think some celebratory activities are called for its not every day our Castiel gets a date what do you kids think?"  
"Dad nothing less than ice cream will do."  
A chorus of agreement came from the back seat.  
"Ok but get something in a bowl I still need to have you guys home in a little while. We are Rainbow Cone bound guys."  
"How fitting!" Cas said and the car's occupants erupted into giggles

"Bye guys! Thanks for the ride Mr. Fitzgerald!" Cas called waving to them from his door step. He let himself into house dropped his book in the hall and went to search for a spoon for his Ice cream. He passed Samandriel who was coloring on the couch he look sad. Two spoons then.

"Hey Alfie what's up?" Cas put the ice cream in his lap and handed him a spoon.  
"Gabriel yelled at me because I spilled legos on the floor when I asked him to play. Castiel it was accident I promise I cleaned them up and everything but Gabe still wont open the door." He sounded near tears.  
"Hey Alfie its ok! We don't need Gabe to play how about you finish this ice cream while I do some homework and then me and you will play till Dad comes home." He pulled Alfie in for a hug. "Sound good?" When he nodded cas sent him into the kitchen so he wouldn't make a mess on the couch and went to get his book bag. He got a decent amount of work done before Alfie came back and they built everything from fram animals to airplanes with legos till Cas got a text from Balthazar.

Balthazar:"Cassie last minute rehearsal for gig please start dinner be home late but before dad not a word to dad Tell Alfie and Gabe hi"  
Cas:"Ok but you owe me I want free tickets to a show of my choice and you're on kitchen and bathroom duty for a week"  
Balthazar:"Yes to tickets but kitchen and laundry duty for a week instead and you have a deal"  
Cas:"Deal"

"Alfie you wanna help me cook? We can make your favorite spaghetti and meatballs."  
"Yummy! Cheesy garlic bread too right you can't have spaghetti without cheesy garlic bread its impossible."  
"Well who am I to argue with that logic come on lets go in the kitchen."

"Hey Cassie Dad texted me he'll be here in 10 remember our deal. What did I make for dinner tonight? Smells great! "  
"Balthazar I made spaghetti and meatballs with Alfie for dinner."  
"Don't forget the cheesy garlic bread Cas its the best part! " Alfie yelled to them from the dining room.

Balthazar went to put his guitar away when Alfie started arguing with Gabe as to why cheesy garlic bread was better than plain garlic bread. Luckily Dad arrived before things got heated because that usually end with a crying Alfie and that was the last thing their father wanted to come home to. 

"Hey kids. Balthazar is dinner ready yet?"  
Balthazar sent cas a pleading look and Cas sighed and nodded  
"Yeah Dad me and Alfie made pasta and garlic bread."  
"Good is the table set?"  
"Gabriel is finishing that up now."  
"Well lets eat shall we."

They all took their places and began passing dishes around so everyone could take their fill. Conversation flowed easily between them. Dad asked about their days and they asked about his. When the conversation did die down to just the scrap of fork and knives against plates Cas decided this would be a good time to bring up Dean. 

"I have some news Dad."  
"Really what is it Castiel?"  
"I was asked out today!"  
"Cassie you dog! Who's the lucky girl?"  
"Shut up Balthazar and for you're information it was a guy."  
"That's great Castiel I hope you have fun."

Dinner wrapped up soon after. It was Cas' turn to help Alfie with bed time and he was sleeping soundly after one chapter of Harry potter and the Sorcerer's Stone he was allowed per night. Ok maybe it was two Cas was always a sucker for Alfie world renown pout and could never say no to it. Unfortunately for him Alfie knew this and was not above using it to get what he wanted with in reason. Cas went to his own room to get ready for bed. With his teeth brushed and in fresh out the dryer pajamas he was all ready to climb under the covers. He grabbed his phone off the dresser to check the alarms and put it on the charger the paused there was a new text for a number he didn't know. It could be Dean he hoped it was.

Dean:"hey Cas! Its Dean so what's the verdict on our date?"  
Cas: Sorry to get back so late My dad said yes see you at school ok


	2. Getting to know each other

Dean was nervous Cas hadn't answer his text last night and that could only mean that he couldn't go or was having second thoughts. Neither option was appealing. He sighed and pushed the covers down. Nothing would change if he sat in bed pouting all morning except if he was late for school or not. He reached to grab his phone off the bed side table trying and failing to stifle the hopeful little voice in his head saying that Cas just didn't see his text and had probably replied by now. That voice was only encouraged by the blinking notification light and so was Dean. He pushed the power and his face lit up almost as bright as the screen

1 new text Castiel

Cas: Sorry to get back so late my dad said yes see you at school ok

Dean: good morning and it's cool I'm glad you can go are you up yet?

Cas: good morning to you as well and yes I have been awake for a while

D: oh early riser? I’m more of a 30 minutes before I have to leave kind of guy

C: yeah it runs on my mom's side of the family and me and Alfie are the ones most like her so that why I was eating cereal and watching Phineas and Ferb at 5:45 in the morning

D: Alfie is your little bro I take it. How old is he my brother Adam loves that show they might be around the same age

C: yeah Alfie is the youngest of 4 all boys he's 8 his real name is Samandriel but that's too much of a mouthful

D: Samandriel poor kid image learning to spell that in pre k lol I've got two younger brothers included Adam i'm the oldest you?

C: two younger brothers Alfie and Gabe one older this ones a kicker Balthazar

Dean couldn't help himself he laughed out loud. He was happily typing a reply when Sam banged on the door yelling for Dean to get his butt down for breakfast. He opened the door meaning to glare at Sam but his smiley faced t-shirt (it was a gift for Adam and Dean would have felt bad for not wearing at least sometimes) coupled with his horrible bedhead and sleepy expression made it look a lot more like a pout.

"Sammy I doubt my cereal will get up and walk away if I'm not on time. I'm taking care of some important business."

"Yeah yeah yeah tell your boyfriend I said hello. Aww Dean Winchester you’re blushing so you were texting him

Dean wanted nothing more than to fade in to the god awful wallpaper that covered the hall. Wait on second thought wiping the smug grin off Sam's face would feel a lot better. "So Kevin told me about this new girl in your class Jessica or Jessie no Jess was it?"

"Shut up Dean." Sam shoved past Dean in an attempt to hide the blush creeping up his face. Dean shoved him right back and took his place at the table as he pulled out his phone again. 

D: hey I've got to get dressed see you at school meet by your locker yeah?

*at school Cas*

Should I just wait till the bell? He didn't say a time did he? What if he doesn't show at all? Would he do that? He just asked me out yesterday, he could be having cold feet already. Why does this always happen to me? How the hell am I’m going to tell Charlie!?

His troubling train of thought was interrupted by a light tap to the door of his locker.

"Thinking about me were you? I can see it all over your face."  
"Shut up Dean!" He tried to play off the blush creeping up his neck. "I was thinking about the 11th Doctor if you must know, he's the only man that matters in my life at the moment."  
“Cas you wound me. I’d like to think I could take your Doctor fellow in a race if I had to. I mean that’s his thing right waving around a screwdriver and telling people to run”  
“Did yo. . . did you watch Doctor Who for me? That’s so . . . that’s really cute Dean”  
Cas smiled and now it was Dean’s turn to hide his blush  
“I just thought that um it had to like be a good show since you you know since you like it so much and I just wanted to give it a try. To see what it was like and if I’d like it. So really I did it for myself if you think about it not that I didn’t like think about you while I watched no I mean I thought about how much you would like it. The show I mean not watching it with me.”

Luckily for Dean the bell rang saving him for digger a deeper hole for himself. 

“Like I said yesterday Winchester you’re really cute when you ramble and for the record I would love to watch Doctor Who with you. I’ll see you later ok, we can eat lunch together I mean if you want.” He closed his locked and started walking away.  
“Hey wait!” Dean grabbed his hand to stop him from leaving. He only held it for a second before he realized what he was doing. “I’m sorry if that wasn’t like ok. I just wanted to um ask if I could walk you to advisory.” Now both boys had a noticeable blush covering their faces.  
"No I mean yes you can walk me to advisory and no I don't mind about the uh hand holding thing." Cas smiled and held out his hand. Dean took it and gave him a hesitant squeeze.  
"I think we both could do with less rambling but hey at least you're cute when you do it Novak." 

The late bell rang and they finally started walking toward Cas’ advisory. The halls were mostly empty except for the occasional speed walking student or teacher. There was a comfortable silence that fell between them, hands swinging softly as they slowly made their continued down the hall. Despite how timeless this moment felt they eventually made it to their destination and it was time to go their separate ways.

Cas sighed “Well this is me Dean. You better put those track skills to use if you want to make it to advisory on time, well at all I guess we’re both kinda late already.” He gave Dean’s hand one last squeeze and went to open the door, “I’ll see you at-” The rest of his sentence was swallowed up by the hug Dean pulled him into.  
“Of course I’ll eat lunch with you Cas. Have a good day.” Then he was off running down the hall to get to class. Cas walked into advisory with the biggest smile Charlie had ever seen on anybody this early in the morning. She didn’t even let him sit down before was all over him for details. 

“Cas I swear to god I will fight you if you don’t tell me right now what’s got you all dreamy.”  
“He hugged me Charlie! He walked me here and we were saying goodbye and he just pulled me in. Chalie he smelled so good and it was so nice, I think I wanted to kiss him. God! We haven’t even gone out yet! I’m hopeless.” Charlie looked about ready to burst and all but attached herself to him in a bone crushing hug.  
“Yeah Cassie you’re hopeless and I’m so happy for you!”

*Same time with Dean*

Dean was amazed at how many flights of stairs there were between his advisory and Cas’. He was panting by the time he made it. He had only just managed to get in the room before the 1st period bell rang. “I’m here Mr. Davison! Don’t mark *pant* me *pant pant* absent.” 

“Oh hello Dean. Yes I know Jo told me you we’re working with another student on a project and would be late. I marked you present, just please check in next time ok?”

“Yes, sir. I’m going to head out class now, bye Mr. Davison!”

If Dean thought that school was boring before nothing compared to how slowly the clock seemed to move during first and second period, but it was finally time for lunch and he would have 45 whole minutes to give Castiel his undivided attention. He was equal parts nervous and excited but he hoped only his excitement showed as he walked toward where Cas sat with his lunch box and some kids Dean didn't know that well. He said hi to be polite as he sat next to Cas.

“Hey Dean this is Garth and that's Ash. They were cramming for the trig yesterday which is why you didn't see them. They’re pretty cool.”

“Only pretty cool Cas, wow I think having the only mullet around would at least rank Ash as awesome.”

“Yeah dude business in the front, party in the back!” 

Dean laughed "Well its awesome to meet you guys. How was the trig by the way I have that today?'

The conversation flowed easily between them and no one even noticed when Dean grabbed Cas’ hand under the table. Well they pretended not to notice by it was kind of hard not to when Cas turned silver shades pinker than he was before.

**Notes for the Chapter:**

> So I set up their school day a lot like mine with block days but I realized not many schools do it like we do so here's Dean's schedule as an example 
> 
> A days   
> Advisory 15 mins   
> 1st period choir 90 mins   
> 2a lunch 45 mins   
> 6b gym 45 mins   
> 3rd period chemistry 90 mins   
> 4th period American studies English 90 mins 
> 
> B days   
> Advisory 15 mins   
> 5th period Latin 90 mins   
> 2a lunch 45 mins   
> 6b gym 45 mins   
> 7th period trigonometry 90 mins   
> 8th period American studies history 90 mins

**Author's Note:**

> Ok what did you think? Up next is some texting between our love birds having lunch together and then the actual date possibly


End file.
